Business · 13 episodes
Money Mindset & Financial Wellbeing for entrepreneurs
Money problems in entrepreneurship are rarely math problems. They're awareness problems, identity problems, and nervous-system problems wearing a spreadsheet costume. Scarlett Stanhope says it plainly: more revenue doesn't fix money stress if the underlying relationship with money hasn't changed. Jack Adler, an NFL Biz Week built for athletes, and founders who've bootstrapped through years of no personal salary all point to the same root issue: you can't manage what you refuse to look at, and most people avoid looking because of what they're afraid it will say about them.
There's real disagreement here about what to do with that fear. Some guests say build systems first — track your customer acquisition cost, know your debt coverage ratio, get a real budget or 'blueprint' as Stanhope calls it, treat your body like a business asset. Others insist the systems won't hold until you deal with the internal wiring — the scarcity seeds, the imposter-syndrome gap between skill and confidence, the inability to trust yourself with your own company's finances. Both camps are right about different failure modes. Founders who skip the psychology stay anxious even when the numbers are fine. Founders who skip the numbers stay anxious because the numbers actually aren't fine.
What nobody disputes: debt, growth, and cash all amplify whatever is already true about you. Leverage helps a disciplined operator and destroys an undisciplined one. A big raise fixes a cash problem but not a self-worth problem. And the entrepreneurs who talk most calmly about money are, without exception, the ones who stopped treating their net worth as a referendum on their character.
What holds across every conversation
- •Before touching investing or growth, get full visibility on your numbers — awareness, not amount of income, is what actually kills money stress.
- •Calculate what it literally costs to be you (or to run your business) per month; most founders and athletes never do this and it's why windfalls disappear.
- •Use a 'blueprint' instead of a restrictive budget: know what you can do with what you have, not just what you can't do.
- •Keep debt payments small enough relative to cash flow that they're never the first thing you think about — if a lender feels like your biggest partner, you're over-leveraged.
- •Separate your net worth from your self-worth explicitly; scarcity thinking (not-enoughness, unworthiness, starving-artist syndrome) drives pricing and hiring decisions more than the market does.
- •When raising money pre-revenue, lead with vision and story — investors are underwriting belief in you, not a defensible valuation.
Why more money doesn't fix stress
The clearest myth-buster in the collection: income and financial peace are not the same variable.
“I've found time and time again that if you're somebody that experiences money stress, more money is not the solution to that problem because I've worked with clients with very little money coming in and they feel stressed... Because it's not about the amount of money, it's about your relationship with money.”
Money Stress, Scarcity & Abundance with Scarlett Stanhope · 13:08· listen →
“I find that one of the number one causes of money stress is actually lack of awareness around your money. Because if you don't know what's happening with your money, if you can't see it clearly, it just puts your brain into the unknown.”
Money Stress, Scarcity & Abundance with Scarlett Stanhope · 26:13· listen →
“Money is the number one cause of stress, especially that low-grade, back-of-the-mind, always there, always thinking about it, that kind of stress. It really keeps your body in a fight-or-flight state all the time. And when you're in that fight-or-flight state, your body is not in regeneration mode.”
Money Stress, Scarcity & Abundance with Scarlett Stanhope · 33:35· listen →
“How much does it cost to be Justin Pugh or whoever's listening right now? Most people at home probably can't even tell you that. The NFL player just had a bunch of money over a very short period of time. And they didn't know how much it costs to be them.”
From NFL to Entrepreneurship: Justin Pugh's Playbook · 10:50· listen →
The scarcity seeds behind bad decisions
Not-enoughness, unworthiness, and starving-artist syndrome show up as pricing decisions, hiring delays, and self-sabotage long before they show up as beliefs.
“The first one is not enoughness. This is the idea that there's not enough to go around... nature proves to us that there is an infinite abundant amount available. For example, if you have one tomato, that tomato is full of seeds to create an infinite future amount of tomato plants.”
Money Stress, Scarcity & Abundance with Scarlett Stanhope · 16:04· listen →
“The third one, and this is especially important for entrepreneurship as well, is starving artist syndrome. This is the idea that we live in an either-or life. Either I can have lots of money and hate my life and be unfulfilled, or I can love what I do, but be broke and be a starving artist, but I can't have both.”
Money Stress, Scarcity & Abundance with Scarlett Stanhope · 20:29· listen →
“A budget tells you what you can't do with what you have. It does feel limiting or restricting, like dieting, but a blueprint tells you what you can do with what you have. It puts the control and the power back in your hands.”
Money Stress, Scarcity & Abundance with Scarlett Stanhope · 29:46· listen →
“Most of us suffer from imposter syndrome, right? Your skill level's going like this, your confidence level's going like that, and there's this gap.”
Matt Read: Building Spatchcock Funk's Media Business · 19:03· listen →
Trusting yourself with the numbers
Distrust of your own financial judgment shows up as avoidance and outsourcing; the fix isn't better software, it's a different relationship to ownership.
“I think that our businesses are physical representation of the inner work that we have to do on ourselves—that's what I found.”
Holly Conti: Scaling to 7 Figures with Mindset Work · 13:20· listen →
“We're also spending about 7 figures. If that's what they don't tell you when you're going after that big goal is that it's not about that big goal at all. It's about the profitability number.”
Holly Conti: Scaling to 7 Figures with Mindset Work · 16:30· listen →
“I was spending money almost like it wasn't my own and treating the money like it wasn't mine... I am the business. Caitlin and I are the business. It is ours.”
Holly Conti: Scaling to 7 Figures with Mindset Work · 17:16· listen →
“By putting too much weight on what you think could or hopefully will happen, you end up I think like almost losing track in what needs to be done right in front of you.”
Jack Adler on Building Out2Win and Raising $1.3M Young · 19:32· listen →
Leverage, debt, and knowing your real cost
Debt and growth capital are neutral tools that only work when a founder actually knows their numbers — coverage ratios, acquisition cost, and what it costs to be them.
“So think about your debt lenders like partners, but also partners that can really turn the screws on your business. If they become an outsized part of your monthly cash flow, that's way too much debt. You want them to be something that is manageable and something that is not the first thing you think of, mainly because your business might maintain over time, but you, if you have debt burden, are so much less likely to take on risk.”
Debt Strategy for Entrepreneurs: Leverage Without Crushing · 0:00· listen →
“Those lenders don't take equity risk. They don't take business operations risk. They don't take like that. They're expecting their payment next month every single time, no matter how much disruption there is in your business. And if you don't have enough cushion over those debt payments that you're planning on making, you're not going to be able to continue to make them, right?”
Debt Strategy for Entrepreneurs: Leverage Without Crushing · 3:50· listen →
“I mean, just the, the, the very first thing, right, that is top of mind is skin in the game, right? There is a big difference between if somebody has money in something, their own money, versus if they have none. Right?”
Debt Strategy for Entrepreneurs: Leverage Without Crushing · 7:46· listen →
“It comes down to acquiring a business. It comes down to how much are you paying to acquire a net new customer, which you take your total advertising spend in a given month divided by about the new customers in the business, and that's your customer acquisition cost, and then the lifetime value of that customer.”
Grayson Cross on Scaling E-Commerce, AI, and Burnout · 9:48· listen →
“And that always stuck with me. It's like, we already did the hard part. We made it to the NFL, which no one thought we could do. You make life-changing money. Let's get really good at saving before we ever get good at investing.”
From NFL to Entrepreneurship: Justin Pugh's Playbook · 8:21· listen →
Raising capital on story, not certainty
Early-stage valuation is guesswork; what actually moves investors is belief in the founder and the vision, not the spreadsheet.
“The valuation is going to always be the most speculative thing you can do in the world... So the 2 tips is find a way to find any way to justify some kind of valuation. But also find investors that are going to believe in what you're doing because creative stuff like might work, it might not.”
Matt Read: Building Spatchcock Funk's Media Business · 47:35· listen →
“So much of it's about storytelling and in a way, vision dumping, because that's what gets people excited. That's what gets people to buy in. And that's a lot of what I was doing in the early stages of raising money. It was really just pitching the vision that I had for where this could go.”
Jack Adler on Building Out2Win and Raising $1.3M Young · 7:37· listen →
“He who do not have the money does not have the choices.”
Lane Kawaoka on Real Estate Wealth Building for Entrepreneurs · 3:30· listen →
The chase that never satisfies
Several guests describe a version of the same trap: treating the next win like a drug, and only escaping it by redefining what winning is actually for.
“If you break yourself down just to be successful in business, it's not even about enjoying the benefits of money and those things, it's about enjoying your life. And, I think that gets lost. We learn about the so-called hustle culture, #hustle. Everybody's like, grind, grind, grind. But, that really isn't accurate.”
Matt Read: Building Spatchcock Funk's Media Business · 2:51· listen →
“That next big win is a weird thing... it's like doing drugs. And when you're doing things like that, you get this high and you're thinking to replicate it. If you keep chasing it that way, it's only going to destroy you.”
Matt Read: Building Spatchcock Funk's Media Business · 4:34· listen →
“Money is energy. It's everywhere. Everybody can be as rich as they wanna be. That is kind of the easy part.”
Ashley Black: Necessity, Near-Death & High Vibration Living · 39:16· listen →
“You know, it was years until I replaced my salary. You know, I think, I think people, I think a lot of people have the wrong idea about entrepreneurship. They think that, oh, you got a business, you must be rolling in the cash, right?”
Jeff Knauss: AI Employees, Bootstrapping & Exit Lessons · 17:35· listen →
The companion guide
Reading about money mindset & financial wellbeing is one thing. Changing it is another.
John’s companion guide turns what these conversations cover into something you can actually work through.
More moments worth hearing
Everything else these conversations turned up on this subject.
“First just make something cool and then worry about how you get it in front of people. It does not work the other way. That's where you see like the Hawktua girl... She had a shot and then didn't do anything with it because she wasn't prepared. So first, prepare your ideas and your cool content, and then worry about getting the people to see it.”
Matt Read: Building Spatchcock Funk's Media Business · 14:58
“I talk to myself sometimes and I would never talk to a friend like that ever. I forgot my flash drive. You piece of shit. Like, how are you not prepared for this? You know? And it's trying to stop yourself from doing that.”
Matt Read: Building Spatchcock Funk's Media Business · 21:50
“I think that's a big mistake with serial entrepreneurship is people see it as diversifying their risk. But because the root cause of startup failure is the internal mismanagement that derails decision-making, what will happen is that you're going to be fighting fires everywhere.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 16:46
“You manage them like you manage a plant. You won't water a plant if it's raining for a week. So, just as you don't have to water your energy if you've been at a Spartan Race boot camp for a week.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 18:50
“It's okay to let the world burn for a while. So, you think you need to fight every fire, but if you let it burn, usually it's not as bad as you think. And then in stillness, you find clarity.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 19:58
“I believe entrepreneurship is a hero journey, which means that you step into the unknown. But the way we're approaching entrepreneurship right now is we're doing it in reverse. We're aiming for tactics, tools, skills that we can plug and play into a trail that's known in our forest.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 21:44
“I think part of the answer is acknowledging that the real treasure is not the exit. It's the broken icons that you had when you started the journey about how it should play out, who you are, what are your skills that are being destroyed by the reality of the experience that you can now integrate into wisdom.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 28:20
“We confuse hustling with business and entrepreneurship. To me, they're all different.”
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention · 26:13
“You don't get the journey you want, you get the journey you need. And so my journey was nothing like what was— nothing came up that gave me any indication about what was next for me. What came up for me were a lot of things from my past that I thought I had processed, but I didn't process.”
David Kahl: From $100M CEO to Psilocybin Guide · 20:26
“After it happened, it was probably the most difficult period of my life. I mean, even more difficult than growing and scaling the company because like, as I said, when you're like, when you're in it, John, you don't realize how much you're in it and how much of your every living drop of energy is going into it.”
David Kahl: From $100M CEO to Psilocybin Guide · 15:57
“So I quit my job that day. I felt it so strongly, John. I knew what was happening and I just didn't want to be there. I'd come off the street with complete strangers feeling a deep connection and I got into this workspace and I was like, this isn't my environment.”
David Kahl: From $100M CEO to Psilocybin Guide · 10:22
“We as entrepreneurs and leaders, that's what gets us where we are, is we think we have this energy above our neck most of the time. We're comparing, we're contrasting, we're judging, doing all the things that make our companies better, that make us better. And so I have to coach them to let go of that and to relax and be vulnerable and release expectations.”
David Kahl: From $100M CEO to Psilocybin Guide · 32:05
“He came out of that journey just crying and very in touch with this realization that he needs to let go more and let people be who they are because they're all, they all have their own ways of expressing love and affection and respect and get out of his own way of how he thought he should be happy.”
David Kahl: From $100M CEO to Psilocybin Guide · 43:12
“It's important just when associating yourself with an athlete and having them represent your brand to the public eye that you just have the full 360 view of like, where are they going to be showing up and how are they going to be showing up? Is this who I want to represent my brand?”
Jack Adler on Building Out2Win and Raising $1.3M Young · 4:28
“It was kind of just this process of feeling out the market, feeling out the feedback that I was constantly receiving. And kind of like you said, just being open-minded, not being stubborn, listening to what people said and taking it, not necessarily taking everything I heard, but recognizing patterns and applying them to where I wanted to take the business.”
Jack Adler on Building Out2Win and Raising $1.3M Young · 6:00
“One of my non-negotiables is working out in the morning. Like before I do anything else, I get up and I work out and that's either a run, that's a lift in the gym, but just like getting my blood flowing in the morning is my form of caffeine.”
Jack Adler on Building Out2Win and Raising $1.3M Young · 17:53
“I just think that there's such an opportunity as a student to go throw yourself into the fire and learn from what most likely will be failure... You have nothing to lose. And now is the time to go out and do it.”
Jack Adler on Building Out2Win and Raising $1.3M Young · 35:10
“The inner voice is the quietest. I think that's what I've learned. And no, I definitely don't always listen to it. No, I think I most often listen to the fear.”
Holly Conti: Scaling to 7 Figures with Mindset Work · 12:18
“I think we feel like I'm failing if I'm not doing it every day. I set a goal and I want to be a meditator, but I do it for a month and then I drop off. So I must not be a meditator. And it's like, well, that was for me years of that before it just slowly became that thing. And that's okay.”
Holly Conti: Scaling to 7 Figures with Mindset Work · 22:28
“I don't think you can always balance all of the time. And I think it's about reducing judgment on yourself.”
Holly Conti: Scaling to 7 Figures with Mindset Work · 36:18
Every episode on money mindset & financial wellbeing
13 conversations, oldest to newest.
Matt Read: Building Spatchcock Funk's Media Business
Chasing the 'next big win' is like chasing a drug high and will eventually destroy you if you never stop to enjoy what you've built.
Phil Neil: Emotional Mastery & Entrepreneurial Reinvention
Three emotions—uncertainty, fear, and unworthiness—derail entrepreneurial decision-making and push founders into a 'shadow' failure zone.
David Kahl: From $100M CEO to Psilocybin Guide
Selling a company can trigger a harder identity crisis than building it, because founders often don't realize how fused their identity is with the business.
Jack Adler on Building Out2Win and Raising $1.3M Young
Jack pivoted his NIL agency into a scalable AI athlete-marketing intelligence platform after recognizing brands lacked data to evaluate athletes as marketers, not just performers.
Holly Conti: Scaling to 7 Figures with Mindset Work
Businesses are a physical representation of the inner work founders do on themselves, so scaling requires addressing limiting beliefs, not just tactics.
From NFL to Entrepreneurship: Justin Pugh's Playbook
Justin Pugh built NFL Biz Week to teach players financial literacy and deal-vetting skills because most athletes retire with no plan and high bankruptcy rates.
From Nazi Orphanage to Vitamin Empire: Charles Van Kessler
Charles survived Nazi persecution, eight years of orphanage abuse, and two years living alone on the streets of Amsterdam before immigrating to America at 22.
Lane Kawaoka on Real Estate Wealth Building for Entrepreneurs
Saving a large income delta is the prerequisite to buying rental properties or starting any capital-intensive business.
Money Stress, Scarcity & Abundance with Scarlett Stanhope
More income doesn't resolve money stress because the problem is an unconscious, emotional relationship with money, not the amount earned.
Grayson Cross on Scaling E-Commerce, AI, and Burnout
Scaling e-commerce brands depends on knowing exact customer acquisition cost and lifetime value rather than guessing based on gut feel.
Debt Strategy for Entrepreneurs: Leverage Without Crushing
Debt is leverage that helps a business grow when used within its cash-flow cushion, but becomes the primary cause of business failure when it exceeds what the business can safely service.
Jeff Knauss: AI Employees, Bootstrapping & Exit Lessons
AI-powered 'digital employees' can absorb administrative work so humans focus on relationships, decisions, and creative high-value tasks.
Ashley Black: Necessity, Near-Death & High Vibration Living
Ashley Black's chronic childhood illness and a near-fatal infection directly led her to invent the Fascia Blaster and build a $200 million company.